EP1130023B1 - Procédé de préparation d'organosilylalkylpolysulfanes - Google Patents
Procédé de préparation d'organosilylalkylpolysulfanes Download PDFInfo
- Publication number
- EP1130023B1 EP1130023B1 EP01103386A EP01103386A EP1130023B1 EP 1130023 B1 EP1130023 B1 EP 1130023B1 EP 01103386 A EP01103386 A EP 01103386A EP 01103386 A EP01103386 A EP 01103386A EP 1130023 B1 EP1130023 B1 EP 1130023B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- added
- reactor
- comparative example
- mixture
- sulfur
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 229910000057 polysulfane Inorganic materials 0.000 title claims description 58
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 72
- 150000004820 halides Chemical class 0.000 claims abstract description 25
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 239000000725 suspension Substances 0.000 claims abstract description 8
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract 3
- 239000011593 sulfur Substances 0.000 claims description 59
- 229910052717 sulfur Inorganic materials 0.000 claims description 59
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 25
- -1 alkylene radical Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 abstract description 2
- 229940006486 zinc cation Drugs 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 100
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 97
- 230000000052 comparative effect Effects 0.000 description 95
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 67
- 239000000047 product Substances 0.000 description 51
- 238000004128 high performance liquid chromatography Methods 0.000 description 48
- 238000002360 preparation method Methods 0.000 description 47
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 42
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 30
- 229910052979 sodium sulfide Inorganic materials 0.000 description 23
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 19
- 239000008187 granular material Substances 0.000 description 16
- 239000005077 polysulfide Substances 0.000 description 16
- 229920001021 polysulfide Polymers 0.000 description 16
- 150000008117 polysulfides Polymers 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 239000003513 alkali Substances 0.000 description 11
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 9
- 150000004763 sulfides Chemical class 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 150000001282 organosilanes Chemical class 0.000 description 4
- 230000002123 temporal effect Effects 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 2
- 229940077464 ammonium ion Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000005425 toluyl group Chemical group 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 125000004826 2,3-dimethylpropylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])(C([H])([H])[H])C([H])([H])[*:1] 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012758 reinforcing additive Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LPSWFOCTMJQJIS-UHFFFAOYSA-N sulfanium;hydroxide Chemical class [OH-].[SH3+] LPSWFOCTMJQJIS-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
Definitions
- Organosilylalkylpolysulfanes are found in the literature described. Processes are the most economical and the easiest alternative to implement that of technically easily accessible Organosilylalkylhalogeniden run out.
- This Organosilane alkyl halides are mixed with ionic Polysulfides implemented by nucleophilic Substitution of the halide functions of two molecules Polysulfan units exchanged and thus with each other get connected.
- the molar ratios of the individual reactants to one another depend on the average length of the sulfur chain in the organosilylalkylpolysulfane (I) to be produced and the residual organosilylalkylhalide (II) content in the end product.
- the molar ratio of the ionic sulfide of the formula (III) to the elemental sulfur used controls the average polysulfane chain length in the end product.
- Ionic sulfide sulfur in a molar ratio of at least 1: 0.1, preferably 1: 0.8, to 1: 5.2 can be used for the process according to the invention.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Silicon Polymers (AREA)
Claims (4)
- Procédé de préparation d'organosilylalkylpolysulfanes de formule générale
R1, R2, R3 , identiques ou différents l'un de l'autre, représentent des groupes alkyle et/ou alcoxy ramifiés ou non ramifiés ayant une longueur de chaíne de 1 à 8 atomes de carbone, ou des restes aryles ayant au moins un groupe alcoxy est présent,
R4 représente un radical alkylène bivalent ayant une longueur de chaíne de 1 à 8 atomes de carbone, ou
x est un nombre supérieur à 1,
par réaction d'un halogénure d'organosilylalkyle de formule générale
R1, R2, R3 et R4 ont la signification indiquée ci-dessus et
X représente chlore, brome ou iode,
et d'un sulfure ionique anhydre ou presque anhydre de formule générale
ainsi que du soufre élémentaire,
caractérisé en ce qu'
on dispose dans un solvant organique polaire le soufre élémentaire et l'halogénure d'organosilylalkyle, et on ajoute à cette suspension le sulfure ionique anhydre ou presque anhydre. - Procédé de préparation d'organosilylalkylpolysulfanes selon la revendication 1,
caractérisé en ce qu'
on utilise un sulfure ionique comportant au maximum 10% en poids d'eau. - Procédé de préparation d'organosilylalkylpolysulfanes selon la revendication 1,
caractérisé en ce que
comme solvants organiques on utilise des alcools linéaires ou ramifiés comportant de 1 à 8 atomes de carbone. - Procédé de préparation d'organosilylalkylpolysulfanes de formule générale
R1, R2, R3, identiques ou différents, représentent des groupe alkyle et/ou alcoxy ramifiés ou non ramifiés ayant une longueur de chaíne de 1 à 8 atomes de carbone, des radicaux aryle, avec au moins un groupe alcoxy présent,
R4 est un n-propylène,
x est un nombre supérieur à 1,
par réaction d'un halogénure d'organosilylalkyle de formule générale
R1, R2, R3 et R4 ont la signification indiquée ci-dessus et
X représente chlore, brome ou iode,
et d'un sulfure ionique anhydre ou presque anhydre de formule générale
ainsi que du soufre élémentaire,
caractérisé en ce qu'
on dispose dans un solvant organique polaire le soufre élémentaire et l'halogénure d'organosilylalkyle, et on ajoute à cette suspension le sulfure ionique anhydre ou presque anhydre.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10009790 | 2000-03-01 | ||
| DE10009790A DE10009790C1 (de) | 2000-03-01 | 2000-03-01 | Verfahren zur Herstellung von Organosilylalkylpolysulfanen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP1130023A2 EP1130023A2 (fr) | 2001-09-05 |
| EP1130023A3 EP1130023A3 (fr) | 2002-09-11 |
| EP1130023B1 true EP1130023B1 (fr) | 2004-08-11 |
Family
ID=7632984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP01103386A Expired - Lifetime EP1130023B1 (fr) | 2000-03-01 | 2001-02-14 | Procédé de préparation d'organosilylalkylpolysulfanes |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6465672B2 (fr) |
| EP (1) | EP1130023B1 (fr) |
| JP (1) | JP4669139B2 (fr) |
| KR (1) | KR100728512B1 (fr) |
| CN (1) | CN1186347C (fr) |
| AT (1) | ATE273311T1 (fr) |
| BR (1) | BR0100803A (fr) |
| CZ (1) | CZ2001684A3 (fr) |
| DE (2) | DE10009790C1 (fr) |
| ES (1) | ES2222279T3 (fr) |
| HU (1) | HU222433B1 (fr) |
| IL (1) | IL141711A (fr) |
| MX (1) | MXPA01002158A (fr) |
| MY (1) | MY133849A (fr) |
| PL (1) | PL346194A1 (fr) |
| RU (1) | RU2259374C2 (fr) |
| TW (1) | TWI232864B (fr) |
| UA (1) | UA68389C2 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1830985B (zh) * | 2005-03-07 | 2012-10-10 | 赢创德固赛有限公司 | 有机硅烷的制备方法 |
| KR101260517B1 (ko) | 2005-03-07 | 2013-05-06 | 에보니크 데구사 게엠베하 | 유기실란의 제조 방법 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10009790C1 (de) | 2000-03-01 | 2001-09-20 | Degussa | Verfahren zur Herstellung von Organosilylalkylpolysulfanen |
| DE102004030737A1 (de) | 2004-06-25 | 2006-01-12 | Degussa Ag | Verfahren und Vorrichtung zur Extraktion von Stoffen aus silanmodifizierten Füllstoffen |
| DE102005020535B3 (de) | 2005-05-03 | 2006-06-08 | Degussa Ag | Verfahren zur Herstellung von Mercaptoorganyl(alkoxysilanen) |
| DE102005037690A1 (de) * | 2005-08-10 | 2007-02-15 | Degussa Ag | Verfahren zur Herstellung von Organosiliciumverbindungen |
| DE102005038791A1 (de) | 2005-08-17 | 2007-02-22 | Degussa Ag | Organosiliciumverbindungen, ihre Herstellung und ihre Verwendung |
| JP2007091677A (ja) * | 2005-09-30 | 2007-04-12 | Shin Etsu Chem Co Ltd | スルフィド鎖含有有機珪素化合物の製造方法 |
| DE102005060122A1 (de) | 2005-12-16 | 2007-06-21 | Degussa Gmbh | Verfahren zur Herstellung von (Mercaptoorganyl)alkylpolyethersilanen |
| DE102006027235A1 (de) | 2006-06-09 | 2008-01-17 | Evonik Degussa Gmbh | Kautschukmischungen |
| DE102006041356A1 (de) | 2006-09-01 | 2008-03-20 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Organosilanen |
| DE102008035623A1 (de) | 2008-07-31 | 2010-02-04 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Organosilanen |
| DE102012108096A1 (de) | 2012-08-31 | 2014-03-06 | Continental Reifen Deutschland Gmbh | Verfahren zur Regenerierung von schwefelvernetzten Gummivulkanisaten zu Regeneraten |
| EP3862359B1 (fr) | 2020-02-06 | 2024-04-03 | Evonik Operations GmbH | Procédé de fabrication de polysulfansilanes |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2141159C3 (de) | 1971-08-17 | 1983-11-24 | Degussa Ag, 6000 Frankfurt | Schwefel enthaltende Organosiliciumverbindungen |
| BE787691A (fr) * | 1971-08-17 | 1973-02-19 | Degussa | Composes organosiliciques contenant du soufre |
| US3978103A (en) * | 1971-08-17 | 1976-08-31 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Sulfur containing organosilicon compounds |
| DE2212239C3 (de) | 1972-03-14 | 1984-03-15 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Schwefel enthaltenden Organosiliciumverbindungen |
| US4048206A (en) | 1975-04-22 | 1977-09-13 | Mikhail Grigorievich Voronkov | Process for the production of 1-organylsilatranes and carbofunctional derivatives thereof |
| US4125552A (en) | 1975-12-29 | 1978-11-14 | Dow Corning Corporation | Preparation of alkyl polysulfides |
| BE893168A (fr) * | 1982-05-13 | 1982-11-16 | Vesuvius Internat Corp | Orifice d'injection d'un gaz de protection dans un tube de coulee |
| JP3543352B2 (ja) * | 1994-02-16 | 2004-07-14 | 信越化学工業株式会社 | 含硫黄有機珪素化合物の製造方法 |
| US5399739A (en) | 1994-04-18 | 1995-03-21 | Wright Chemical Corporation | Method of making sulfur-containing organosilanes |
| US5468893A (en) | 1994-07-08 | 1995-11-21 | The Goodyear Tire & Rubber Company | Preparation of sulfur-containing organosilicon compounds |
| US5489701A (en) | 1994-09-28 | 1996-02-06 | Osi Specialties, Inc. | Process for the preparation of silane polysulfides |
| US5583245A (en) | 1996-03-06 | 1996-12-10 | The Goodyear Tire & Rubber Company | Preparation of sulfur-containing organosilicon compounds |
| DE19610281A1 (de) | 1996-03-15 | 1997-09-18 | Bayer Ag | Verfahren zur Herstellung von polysulfidischen Silylethern |
| US5663396A (en) | 1996-10-31 | 1997-09-02 | The Goodyear Tire & Rubber Company | Preparation of sulfur-containing organosilicon compounds |
| DE19651849A1 (de) * | 1996-12-13 | 1998-06-18 | Degussa | Verfahren zur Herstellung von Bis(silylorganyl)-polysulfanen |
| DE19734295C1 (de) * | 1997-08-08 | 1999-02-25 | Degussa | Verfahren zur Herstellung von Organosiliciumdisulfanen hoher Reinheit |
| JP3498559B2 (ja) * | 1997-12-01 | 2004-02-16 | 信越化学工業株式会社 | 短鎖ポリスルフィドシラン混合物の製造方法 |
| JP3501008B2 (ja) * | 1998-04-10 | 2004-02-23 | ダイソー株式会社 | 含硫黄有機珪素化合物の製造方法およびその合成中間体の製造方法 |
| DE19819373A1 (de) * | 1998-04-30 | 1999-11-04 | Degussa | Verfahren zur Herstellung von Gemischen von Organosiliciumoligosulfanen mit einem hohen Anteil an Organanosiliciumdisulfanen |
| JPH11349594A (ja) * | 1998-06-08 | 1999-12-21 | Shin Etsu Chem Co Ltd | 短鎖ポリスルフィドシラン混合物の製造方法 |
| DE19930495C1 (de) * | 1999-07-01 | 2000-11-09 | Degussa | Verfahren zur Herstellung von polysulfidischen Silanverbindungen |
| DE10009790C1 (de) | 2000-03-01 | 2001-09-20 | Degussa | Verfahren zur Herstellung von Organosilylalkylpolysulfanen |
-
2000
- 2000-03-01 DE DE10009790A patent/DE10009790C1/de not_active Expired - Fee Related
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2001
- 2001-02-14 EP EP01103386A patent/EP1130023B1/fr not_active Expired - Lifetime
- 2001-02-14 ES ES01103386T patent/ES2222279T3/es not_active Expired - Lifetime
- 2001-02-14 DE DE50103173T patent/DE50103173D1/de not_active Expired - Fee Related
- 2001-02-14 AT AT01103386T patent/ATE273311T1/de not_active IP Right Cessation
- 2001-02-22 CZ CZ2001684A patent/CZ2001684A3/cs unknown
- 2001-02-26 TW TW090104368A patent/TWI232864B/zh not_active IP Right Cessation
- 2001-02-26 JP JP2001051228A patent/JP4669139B2/ja not_active Expired - Fee Related
- 2001-02-28 MY MYPI20010912A patent/MY133849A/en unknown
- 2001-02-28 IL IL14171101A patent/IL141711A/en not_active IP Right Cessation
- 2001-02-28 PL PL01346194A patent/PL346194A1/xx not_active IP Right Cessation
- 2001-02-28 RU RU2001105473/04A patent/RU2259374C2/ru not_active IP Right Cessation
- 2001-02-28 MX MXPA01002158A patent/MXPA01002158A/es unknown
- 2001-02-28 KR KR1020010010305A patent/KR100728512B1/ko not_active IP Right Cessation
- 2001-02-28 HU HU0100921A patent/HU222433B1/hu not_active IP Right Cessation
- 2001-03-01 US US09/795,709 patent/US6465672B2/en not_active Expired - Lifetime
- 2001-03-01 CN CNB011043857A patent/CN1186347C/zh not_active Expired - Fee Related
- 2001-03-01 UA UA2001031439A patent/UA68389C2/uk unknown
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1830985B (zh) * | 2005-03-07 | 2012-10-10 | 赢创德固赛有限公司 | 有机硅烷的制备方法 |
| KR101260517B1 (ko) | 2005-03-07 | 2013-05-06 | 에보니크 데구사 게엠베하 | 유기실란의 제조 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| MY133849A (en) | 2007-11-30 |
| ES2222279T3 (es) | 2005-02-01 |
| MXPA01002158A (es) | 2002-11-29 |
| HU222433B1 (hu) | 2003-07-28 |
| RU2259374C2 (ru) | 2005-08-27 |
| JP4669139B2 (ja) | 2011-04-13 |
| ATE273311T1 (de) | 2004-08-15 |
| IL141711A0 (en) | 2002-03-10 |
| HUP0100921A2 (hu) | 2001-12-28 |
| BR0100803A (pt) | 2001-11-06 |
| JP2001270886A (ja) | 2001-10-02 |
| EP1130023A3 (fr) | 2002-09-11 |
| KR20010086591A (ko) | 2001-09-13 |
| CN1311187A (zh) | 2001-09-05 |
| UA68389C2 (en) | 2004-08-16 |
| US20010037034A1 (en) | 2001-11-01 |
| US6465672B2 (en) | 2002-10-15 |
| CN1186347C (zh) | 2005-01-26 |
| CZ2001684A3 (cs) | 2001-10-17 |
| DE50103173D1 (de) | 2004-09-16 |
| HU0100921D0 (en) | 2001-05-28 |
| TWI232864B (en) | 2005-05-21 |
| IL141711A (en) | 2004-02-19 |
| KR100728512B1 (ko) | 2007-06-15 |
| DE10009790C1 (de) | 2001-09-20 |
| EP1130023A2 (fr) | 2001-09-05 |
| PL346194A1 (en) | 2001-09-10 |
| HUP0100921A3 (en) | 2002-05-28 |
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